KR20110025676A - Fungicidal composition and method for controlling plant diseases - Google Patents
Fungicidal composition and method for controlling plant diseases Download PDFInfo
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Abstract
본 발명은 식물 병원균에 기인하는 식물 병해에 감염된 재배 작물에 대한 안정되고 높은 살진균 효과를 가지는 살진균제 조성물을 제공한다.
본 발명의 살진균제 조성물은 (a) 화학식 I로 표시되는 벤조일피리딘 유도체 또는 그의 염과 (b) 적어도 1종의 다른 살진균제를 유효 성분으로서 함유하는 것을 특징으로 한다.
<화학식 I>
[식 중, A가 -N=인 경우, B는 -CX4=이고; A가 -CH=인 경우, B는 -N=이고; X1 및 X2는 각각 독립적으로 할로겐 원자, 알콕시기, 수산기, 알킬기, CF3기 또는 알킬티오기이고; X3은 수소 원자, 할로겐 원자, 알콕시기, 알킬기, CF3기 또는 알킬티오기이고; X4는 수소 원자, 할로겐 원자, 알콕시기, 알킬기, CF3기 또는 알킬티오기이고; R1은 알킬기이고; R2'은 알콕시기이고; p는 0, 1 또는 2이고; R2'' 및 R2'''은 각각 알콕시기임]The present invention provides fungicide compositions having a stable and high fungicidal effect on cultivated crops infected with plant diseases caused by plant pathogens.
The fungicide composition of the present invention is characterized by containing (a) a benzoylpyridine derivative represented by the formula (I) or a salt thereof and (b) at least one other fungicide as an active ingredient.
<Formula I>
[Wherein A is -N =, B is -CX 4 =; When A is -CH =, B is -N =; X 1 and X 2 are each independently a halogen atom, an alkoxy group, a hydroxyl group, an alkyl group, a CF 3 group or an alkylthio group; X 3 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF 3 group or an alkylthio group; X 4 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF 3 group or an alkylthio group; R 1 is an alkyl group; R 2 ' is an alkoxy group; p is 0, 1 or 2; R 2 '' and R 2 ''' are each an alkoxy group]
Description
본 발명은 식물 병해를 예방 및/또는 치료하는 효과를 각별히 향상시킨 농원예용 살진균제로서 유용한 살진균제 조성물 및 그 조성물을 이용하는 식물 병해의 방제 방법에 관한 것이다.The present invention relates to fungicide compositions useful as agricultural and horticultural fungicides which have significantly improved the effects of preventing and / or treating plant diseases, and a method for controlling plant diseases using the composition.
특허문헌 1에는 본 발명의 살진균제 조성물의 유효 성분인 벤조일피리딘 유도체가 살진균제로서 유용하다는 것이 기재되어 있고, 필요에 따라서 다른 살진균제와의 병용이 가능하다는 기재가 있다. 또한, 특허문헌 2에는 다른 살진균제와의 병용에 의해 현저히 우수한 상승 효과를 가지는 살진균제 조성물이 얻어진다는 것이 기재되어 있다. 그러나, 본 발명의 특정 조합의 조성물이 현저히 우수한 살진균 효과를 갖는다는 것은 알려져 있지 않았다.Patent Document 1 discloses that a benzoylpyridine derivative, which is an active ingredient of the fungicide composition of the present invention, is useful as a fungicide, and there is a description that combination with other fungicides is possible if necessary. In addition, Patent Document 2 describes that a fungicide composition having a remarkably excellent synergistic effect is obtained by use with other fungicides. However, it is not known that compositions of certain combinations of the present invention have significantly superior fungicidal effects.
후술하는 화학식 I로 표시되는 벤조일피리딘 유도체는, 각각 그의 식물 병해 방제 효과에서 특정한 식물 병해에 대하여 그 효과가 충분하지 않거나, 잔효성이 비교적 짧거나, 내우성이 약하거나 하여, 특정 시용 장면에서는 식물 병해에 대하여 실용상, 불충분한 방제 효과 밖에 나타나지 않는 경우도 있다.The benzoylpyridine derivative represented by the formula (I) to be described later is a plant in a specific application scene because its effect is not sufficient for a particular plant disease in its plant disease control effect, or its residual activity is relatively short or its rain resistance is weak. In practice, there may be only insufficient control effects against the disease.
본 발명자들은 상술한 문제점을 해결하기 위해 연구한 결과, 후술하는 화학식 I로 표시되는 벤조일피리딘 유도체와 특정한 살진균제를 병용하면, 각 화합물을 단독으로 사용한 경우에 비해, 예상할 수 없는 우수한 살진균 효과가 얻어진다는 지견을 얻어서, 본 발명을 완성하였다.The present inventors have studied to solve the above problems, and as a result, when using a benzoylpyridine derivative represented by the following formula (I) and a specific fungicide in combination, compared to the case of using each compound alone, the unexpected fungicidal effect The knowledge was obtained that the present invention was completed, and this invention was completed.
즉, 본 발명은 (a) 화학식 I로 표시되는 벤조일피리딘 유도체 또는 그의 염과 (b) 피라클로스트로빈, 보스칼리드, 펜티오피라드, 피리벤카르브, 멥틸디노캅, 디페노코나졸, 도딘, 황, 플루티아닐, 6-t-부틸-8-플루오로-2,3-디메틸퀴놀린-4-일 아세테이트 및 화학식 II로 표시되는 화합물로 이루어지는 군에서 선택되는 적어도 1종의 살진균제를 유효 성분으로서 함유하는 것을 특징으로 하는 살진균제 조성물에 관한 것이다. That is, the present invention provides a composition comprising (a) a benzoylpyridine derivative represented by formula (I) or a salt thereof, and (b) pyraclostrobin, boscalid, penthiopyrad, pyribencarb, meptyldinocap, difenoconazol, dodine, At least one fungicide selected from the group consisting of sulfur, flutianil, 6-t-butyl-8-fluoro-2,3-dimethylquinolin-4-yl acetate and a compound represented by formula (II) is an active ingredient It relates to a fungicide composition characterized in that it contains as.
<화학식 I><Formula I>
[식 중, A가 -N=인 경우, B는 -CX4=이고; A가 -CH=인 경우, B는 -N=이고; X1 및 X2는 각각 독립적으로 할로겐 원자, 알콕시기, 수산기, 알킬기, CF3기 또는 알킬티오기이고; X3은 수소 원자, 할로겐 원자, 알콕시기, 알킬기, CF3기 또는 알킬티오기이고; X4는 수소 원자, 할로겐 원자, 알콕시기, 알킬기, CF3기 또는 알킬티오기이고; R1은 알킬기이고; R2'은 알콕시기이고; p는 0, 1 또는 2이고; R2'' 및 R2'''은 각각 알콕시기임][Wherein A is -N =, B is -CX 4 =; When A is -CH =, B is -N =; X 1 and X 2 are each independently a halogen atom, an alkoxy group, a hydroxyl group, an alkyl group, a CF 3 group or an alkylthio group; X 3 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF 3 group or an alkylthio group; X 4 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF 3 group or an alkylthio group; R 1 is an alkyl group; R 2 ' is an alkoxy group; p is 0, 1 or 2; R 2 '' and R 2 ''' are each an alkoxy group]
<화학식 II><Formula II>
또한, 본 발명은 상기 살진균제 조성물을 식물에 시용하는 것을 포함하는, 식물 병해의 방제 방법에 관한 것이다.The present invention also relates to a method for controlling plant diseases, comprising applying the fungicide composition to a plant.
화학식 I 중의 할로겐 원자로서는 불소, 염소, 브롬, 요오드가 이용되고, 바람직하게는 예를 들면 불소, 염소, 브롬이 이용된다.As the halogen atom in the formula (I), fluorine, chlorine, bromine and iodine are used, and for example, fluorine, chlorine and bromine are used.
화학식 I 중의 알킬기, 알콕시기, 알킬티오기의 알킬 부분으로서는 C1 -6 알킬(예를 들면 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸, t-부틸 등)이 바람직하고, 그 중에서도 C1 -4 알킬이 바람직하다.As the alkyl group in the formula (I), the alkyl portion of an alkoxy group, an alkylthio group, and C 1 -6 alkyl (e.g. methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t- butyl and the like) are preferred, particularly C the 1-4 alkyl is preferred.
화학식 I로 표시되는 벤조일피리딘 유도체는 산성 물질과 함께 염을 형성할 수 있고, 예를 들면 염산염, 브롬화수소산염, 인산염, 황산염 또는 질산염과 같은 무기산염; 아세트산염, 벤조산염, p-톨루엔술폰산염, 메탄술폰산염 또는 프로판술폰산염과 같은 유기산염을 형성할 수 있다.Benzoylpyridine derivatives represented by formula (I) can form salts with acidic materials, for example inorganic salts such as hydrochloride, hydrobromide, phosphate, sulfate or nitrate; Organic acid salts such as acetates, benzoates, p-toluenesulfonates, methanesulfonates or propanesulfonates.
화학식 I로 표시되는 벤조일피리딘 유도체는 상기 특허문헌 1 및 특허문헌 2에 개시된 제조 방법에 의해 얻을 수 있다. 또한, 문헌 [Journal of Organic Chemistry., 58, 7832(1993); 및 European Journal of Organic Chemistry., 7, 1371-1376(2001)]에 준한 방법으로도 제조할 수 있다.The benzoylpyridine derivative represented by general formula (I) can be obtained by the manufacturing method disclosed in the said patent document 1 and patent document 2. See also Journal of Organic Chemistry., 58, 7832 (1993); And European Journal of Organic Chemistry., 7, 1371-1376 (2001).
상기 화학식 I로 표시되는 벤조일피리딘 유도체 또는 그의 염과 배합되는 (b)의 살진균제로서는, 피라클로스트로빈(Pyraclostrobin), 보스칼리드(Boscalid), 펜티오피라드(Penthiopyrad), 피리벤카르브(Pyribencarb), 멥틸디노캅(Meptyldinocap), 디페노코나졸(Difenoconazole), 도딘(Dodine), 황(Sulfur), 플루티아닐(flutianil), 6-t-부틸-8-플루오로-2,3-디메틸퀴놀린-4-일 아세테이트 및 화학식 II로 표시되는 화합물로 이루어지는 군에서 선택되는 적어도 1종의 살진균제를 들 수 있다.As a fungicide of (b) combined with the benzoylpyridine derivative represented by the above formula (I) or a salt thereof, pyraclostrobin, Boscalid, Penthiopyrad, Pyribencarb ), Meptyldinocap, Difenoconazole, Dodine, Sulfur, Flutianil, 6-t-butyl-8-fluoro-2,3-dimethylquinoline And at least one fungicide selected from the group consisting of -4-yl acetate and a compound represented by the formula (II).
<화학식 II><Formula II>
상기 (b)의 살진균제인 피라클로스트로빈은 문헌 [The Pesticide Manual(제14판; BRITISH CROP PROTECTION COUNCIL) 제 900 내지 901 페이지]에 기재된 화합물이다. 보스칼리드는 문헌 [The Pesticide Manual(제14판; BRITISH CROP PROTECTION COUNCIL) 제 110 페이지]에 기재된 화합물이다. 펜티오피라드는 문헌 [The Pesticide Manual(제14판; BRITISH CROP PROTECTION COUNCIL) 제 811 페이지]에 기재된 화합물이다. 피리벤카르브는 문헌 [AG CHEM NEW COMPOUND REVIEW, VOLUME 25, 2007 제 58 페이지]에 기재된 화합물이다. 멥틸디노캅은 문헌 [The Pesticide Manual(제14판; BRITISH CROP PROTECTION COUNCIL) 제 356 내지 358 페이지]에 기재된 화합물이다. 디페노코나졸은 문헌 [The Pesticide Manual(제14판; BRITISH CROP PROTECTION COUNCIL) 제 323 내지 325 페이지]에 기재된 화합물이다. 도딘은 문헌 [The Pesticide Manual(제14판; BRITISH CROP PROTECTION COUNCIL) 제 381 내지 382 페이지]에 기재된 화합물이다. 황은 문헌 [The Pesticide Manual(제14판; BRITISH CROP PROTECTION COUNCIL) 제 978 내지 979 페이지]에 기재된 화합물이다. 플루티아닐은 ISO 1750으로서 잠정 등록되어 있는 화합물이고, 그의 CAS No.는 958647-10-4이다. 6-t-부틸-8-플루오로-2,3-디메틸퀴놀린-4-일 아세테이트는 WO 98/55460의 표 1에 화합물 No. 84로서 기재되어 있는 4-퀴놀리놀 유도체이다. 또한, 상기 화학식 II의 화합물은 문헌 [AG CHEM NEW COMPOUND REVIEW, VOLUME 25, 2007 제 14 페이지]에 CAS No. 214706-53-3으로서 기재된 화합물이다.Pyraclostrobin, the fungicide of (b), is a compound described in The Pesticide Manual (14th edition; BRITISH CROP PROTECTION COUNCIL) pages 900-901. Boscalid is a compound described in The Pesticide Manual (14th edition; BRITISH CROP PROTECTION COUNCIL, page 110). Penthiopyrad is the compound described in The Pesticide Manual (14th edition; BRITISH CROP PROTECTION COUNCIL, page 811). Pyribencarb is a compound described in AG CHEM NEW COMPOUND REVIEW, VOLUME 25, page 58, 2007. The meptyldinocap is a compound described in The Pesticide Manual (14th edition; pages 356 to 358 of BRITISH CROP PROTECTION COUNCIL). Diphenoconazole is a compound described in The Pesticide Manual (14th edition; pages 323-325 of BRITISH CROP PROTECTION COUNCIL). Dodin is a compound described in The Pesticide Manual (14th edition; BRITISH CROP PROTECTION COUNCIL) pages 381-382. Sulfur is a compound described in The Pesticide Manual (14th edition; pages 978 to 979) of BRITISH CROP PROTECTION COUNCIL. Flutianil is a compound that is tentatively registered as ISO 1750, and its CAS No. is 958647-10-4. 6-t-butyl-8-fluoro-2,3-dimethylquinolin-4-yl acetate is described in Table 1 of WO 98/55460. 4-quinolinol derivatives described as 84. In addition, the compound of formula (II) is described in AG CHEM NEW COMPOUND REVIEW, VOLUME 25, page 14, 2007. It is the compound described as 214706-53-3.
본 발명의 살진균제 조성물은 식물 병해에 감염된 재배 작물에 대한 안정되고 높은 살진균 효과를 가지는 것이고, 이 조성물을 이용하여 식물 병해를 방제할 수 있다.The fungicide composition of the present invention has a stable and high fungicidal effect on cultivated crops infected with plant diseases, and the composition can be used to control plant diseases.
화학식 I로 표시되는 벤조일피리딘 유도체에는 A가 -CH=이고 B가 -N=인 경우의 화합물, 즉 화학식 I-1로 표시되는 화합물과, A가 -N=이고, B는 -CX4=인 경우의 화합물, 즉 화학식 I-2로 표시되는 화합물이 있다.The benzoylpyridine derivative represented by Formula (I) includes a compound in which A is -CH = and B is -N =, that is, a compound represented by Formula (I-1), A is -N =, and B is -CX 4 = And compounds represented by the formula (I-2).
<화학식 I-1><Formula I-1>
[X1, X2, X3, R1, R2', R2'' 및 R2'''은 상술한 바와 같음][X 1 , X 2 , X 3 , R 1 , R 2 ' , R 2'' and R 2''' are as described above]
<화학식 I-2><Formula I-2>
[X1, X2, X3, X4, R1, R2', R2'' 및 R2'''은 상술한 바와 같음][X 1 , X 2 , X 3 , X 4 , R 1 , R 2 ' , R 2'' and R 2''' are as described above]
상기 화학식 I-1로 표시되는 화합물 중에서는 3-(2,3,4-트리메톡시-6-메틸벤조일)-4-브로모-5-클로로-2-메톡시피리딘(화합물 No. 1), 3-(2,3,4-트리메톡시-6-메틸벤조일)-5-클로로-4-에틸-2-메톡시피리딘(화합물 No. 2), 3-(4,5-디메톡시-2-메틸벤조일)-4,5-디클로로-2-메톡시피리딘(화합물 No. 3), 3-(5-에톡시-4-메톡시-2-메틸벤조일)-4,5-디클로로-2-메톡시피리딘(화합물 No. 4), 3-(2,3,4-트리메톡시-6-메틸벤조일)-4-브로모-5-클로로-2-에톡시피리딘(화합물 No. 5), 3-(2,3,4-트리메톡시-6-메틸벤조일)-5-클로로-2-에톡시-4-메틸피리딘(화합물 No. 6), 3-(2,3,4-트리메톡시-6-메틸벤조일)-5-브로모-4-클로로-2-에톡시피리딘(화합물 No. 7), 3-(2,3,4-트리메톡시-6-메틸벤조일)-4-클로로-5-요오도-2-메톡시피리딘(화합물 No. 8), 3-(2,3,4-트리메톡시-6-메틸벤조일)-5-요오도-2,4-디메톡시피리딘(화합물 No. 9), 3-(2,3,4-트리메톡시-6-메틸벤조일)-5-클로로-2-메톡시-4-메틸티오피리딘(화합물 No. 10), 3-(2,3,4-트리메톡시-6-메틸벤조일)-5-클로로-2,4-디메톡시피리딘(화합물 No. 11), 3-(2,3,4-트리메톡시-6-메틸벤조일)-4,5-디브로모-2-메톡시피리딘(화합물 No. 12), 3-(2,3,4-트리메톡시-6-메틸벤조일)-4-브로모-2-메톡시-5-메틸피리딘(화합물 No. 13), 3-(2,3,4-트리메톡시-6-메틸벤조일)-5-브로모-4-트리플루오로메틸-2-메톡시피리딘(화합물 No. 14), 3-(2,3,4-트리메톡시-6-메틸벤조일)-4,5-디클로로-2-메톡시피리딘(화합물 No. 15), 3-(2,3,4-트리메톡시-6-메틸벤조일)-2,4-디클로로-5-메틸피리딘(화합물 No. 16), 3-(2,3,4-트리메톡시-6-메틸벤조일)-2,4-디클로로-5-요오도피리딘(화합물 No. 17), 3-(2,3,4-트리메톡시-6-메틸벤조일)-2-플루오로-4-요오도-5-메틸피리딘(화합물 No. 18), 3-(2,3,4-트리메톡시-6-메틸벤조일)-2-플루오로-4,5-디메틸피리딘(화합물 No. 19), 3-(2,3,4-트리메톡시-6-메틸벤조일)-2-메톡시-4,5-디메틸피리딘(화합물 No. 20), 3-(2-에톡시-3,4-디메톡시-6-메틸벤조일)-2-에톡시-4,5-디메틸피리딘(화합물 No. 21), 3-(2,3,4-트리메톡시-6-메틸벤조일)-4,5-디메틸-2-메틸티오피리딘(화합물 No. 22), 3-(2,3,4-트리메톡시-6-메틸벤조일)-5-브로모-4-클로로-2-메톡시피리딘(화합물 No. 23), 3-(2,3,4-트리메톡시-6-메틸벤조일)-4-클로로-2-메톡시-5-메틸피리딘(화합물 No. 24), 3-(2,3,4-트리메톡시-6-메틸벤조일)-2-클로로-5-트리플루오로메틸-4-메틸피리딘(화합물 No. 25), 3-(2,3,4-트리메톡시-6-메틸벤조일)-5-트리플루오로메틸-2-메톡시-4-메틸피리딘(화합물 No. 26), 3-(2,3,4-트리메톡시-6-메틸벤조일)-2,4-디클로로-5-트리플루오로메틸피리딘(화합물 No. 27), 3-(2,3,4-트리메톡시-6-메틸벤조일)-4-클로로-5-트리플루오로메틸-2-메톡시피리딘(화합물 No. 28), 3-(2,3,4-트리메톡시-6-메틸벤조일)-5-클로로-4-에티닐-2-메톡시피리딘(화합물 No. 29), 3-(2,3,4-트리메톡시-6-메틸벤조일)-5-클로로-4-플루오로메틸-2-메톡시피리딘(화합물 No. 30), 3-(2,3,4-트리메톡시-6-메틸벤조일)-5-브로모-4-플루오로메틸-2-메톡시피리딘(화합물 No. 31), 3-(2,3,4-트리메톡시-6-메틸벤조일)-4-플루오로메틸-2-메톡시-5-메틸피리딘(화합물 No. 32), 3-(2,3,4-트리메톡시-6-메틸벤조일)-5-클로로-4-디플루오로메틸-2-메톡시피리딘(화합물 No. 33), 3-(2,3,4-트리메톡시-6-메틸벤조일)-5-에틸-4-트리플루오로메틸-2-메톡시피리딘(화합물 No. 34), 3-(2,3,4-트리메톡시-6-메틸벤조일)-5-클로로-2-메톡시-4-메틸피리딘(화합물 No. 35), 3-(2,3,4-트리메톡시-6-메틸벤조일)-5-브로모-2-메톡시-4-메틸피리딘(화합물 No. 36), 3-(2,3,4-트리메톡시-6-메틸벤조일)-4-트리플루오로메틸-2-메톡시-5-메틸피리딘(화합물 No. 37) 및 3-(4,5-디메톡시-2-메틸벤조일)-5-클로로-2-메톡시-4-메틸피리딘(화합물 No. 38)으로 이루어지는 군에서 선택되는 적어도 1종의 화합물을 이용하는 것이 더욱 바람직하다. 이들 중에서도, 3-(2,3,4-트리메톡시-6-메틸벤조일)-5-클로로-2-메톡시-4-메틸피리딘이 가장 바람직하다.Among the compounds represented by the formula (I-1), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -4-bromo-5-chloro-2-methoxypyridine (Compound No. 1) , 3- (2,3,4-trimethoxy-6-methylbenzoyl) -5-chloro-4-ethyl-2-methoxypyridine (Compound No. 2), 3- (4,5-dimethoxy- 2-methylbenzoyl) -4,5-dichloro-2-methoxypyridine (Compound No. 3), 3- (5-ethoxy-4-methoxy-2-methylbenzoyl) -4,5-dichloro-2 -Methoxypyridine (Compound No. 4), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -4-bromo-5-chloro-2-ethoxypyridine (Compound No. 5) , 3- (2,3,4-trimethoxy-6-methylbenzoyl) -5-chloro-2-ethoxy-4-methylpyridine (Compound No. 6), 3- (2,3,4-tri Methoxy-6-methylbenzoyl) -5-bromo-4-chloro-2-ethoxypyridine (Compound No. 7), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -4 -Chloro-5-iodo-2-methoxypyridine (Compound No. 8), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -5-iodo-2,4-dimethoxy Pyridine (Compound No. 9), 3- (2,3, 4-trimethoxy-6-methylbenzoyl) -5-chloro-2-methoxy-4-methylthiopyridine (Compound No. 10), 3- (2,3,4-trimethoxy-6-methylbenzoyl ) -5-chloro-2,4-dimethoxypyridine (Compound No. 11), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -4,5-dibromo-2-meth Toxypyridine (Compound No. 12), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -4-bromo-2-methoxy-5-methylpyridine (Compound No. 13), 3 -(2,3,4-trimethoxy-6-methylbenzoyl) -5-bromo-4-trifluoromethyl-2-methoxypyridine (Compound No. 14), 3- (2,3,4 -Trimethoxy-6-methylbenzoyl) -4,5-dichloro-2-methoxypyridine (Compound No. 15), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -2, 4-dichloro-5-methylpyridine (Compound No. 16), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -2,4-dichloro-5-iodopyridine (Compound No. 17 ), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -2-fluoro-4-iodo-5-methylpyridine (Compound No. 18), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -2-fluoro-4,5-dimethylpyridine (Compound No. 19), 3- (2,3,4-tri Methoxy-6-methylbenzoyl) -2-methoxy-4,5-dimethylpyridine (Compound No. 20), 3- (2-ethoxy-3,4-dimethoxy-6-methylbenzoyl) -2- Ethoxy-4,5-dimethylpyridine (Compound No. 21), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -4,5-dimethyl-2-methylthiopyridine (Compound No. 22), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -5-bromo-4-chloro-2-methoxypyridine (Compound No. 23), 3- (2,3, 4-trimethoxy-6-methylbenzoyl) -4-chloro-2-methoxy-5-methylpyridine (Compound No. 24), 3- (2,3,4-trimethoxy-6-methylbenzoyl) 2-Chloro-5-trifluoromethyl-4-methylpyridine (Compound No. 25), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -5-trifluoromethyl-2 -Methoxy-4-methylpyridine (Compound No. 26), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -2,4-dichloro-5-trifluoromethylpyridine (Compound No. 27), 3- (2,3,4-trimethock Cy-6-methylbenzoyl) -4-chloro-5-trifluoromethyl-2-methoxypyridine (Compound No. 28), 3- (2,3,4-trimethoxy-6-methylbenzoyl)- 5-Chloro-4-ethynyl-2-methoxypyridine (Compound No. 29), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -5-chloro-4-fluoromethyl- 2-methoxypyridine (Compound No. 30), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -5-bromo-4-fluoromethyl-2-methoxypyridine (Compound No. 31), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -4-fluoromethyl-2-methoxy-5-methylpyridine (Compound No. 32), 3- (2, 3,4-trimethoxy-6-methylbenzoyl) -5-chloro-4-difluoromethyl-2-methoxypyridine (Compound No. 33), 3- (2,3,4-trimethoxy- 6-methylbenzoyl) -5-ethyl-4-trifluoromethyl-2-methoxypyridine (Compound No. 34), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -5- Chloro-2-methoxy-4-methylpyridine (Compound No. 35), 3- (2,3,4-trimethoxy-6-methylbenzoyl) -5-bromo-2-methoxy-4-methylpyridine (Compound No. 36), 3- (2,3, 4-trimethoxy-6-methylbenzoyl) -4-trifluoromethyl-2-methoxy-5-methylpyridine (Compound No. 37) and 3- (4,5-dimethoxy-2-methylbenzoyl) More preferably, at least one compound selected from the group consisting of -5-chloro-2-methoxy-4-methylpyridine (Compound No. 38) is used. Among these, 3- (2,3,4-trimethoxy-6-methylbenzoyl) -5-chloro-2-methoxy-4-methylpyridine is most preferred.
상기 화학식 I-2로 표시되는 화합물 중에서는 4-(2,3,4-트리메톡시-6-메틸벤조일)-2,5-디클로로-3-트리플루오로메틸피리딘(화합물 No. 39), 4-(2,3,4-트리메톡시-6-메틸벤조일)-2-클로로-3-트리플루오로메틸-5-메톡시피리딘(화합물 No. 40), 4-(2,3,4-트리메톡시-6-메틸벤조일)-2-브로모-3-트리플루오로메틸-5-메톡시피리딘(화합물 No. 41), 4-(2,3,4-트리메톡시-6-메틸벤조일)-2,3,5-트리클로로피리딘(화합물 No. 42), 4-(2,3,4-트리메톡시-6-메틸벤조일)-3,5-디클로로피리딘(화합물 No. 43), 4-(2,3,4-트리메톡시-6-메틸벤조일)-3-클로로-5-메톡시피리딘(화합물 No. 44), 4-(2,3,4-트리메톡시-6-메틸벤조일)-2-브로모-3-클로로-5-메톡시피리딘(화합물 No. 45) 및 4-(2,3,4-트리메톡시-6-메틸벤조일)-3-브로모-5-메틸피리딘(화합물 No. 46)으로 이루어지는 군에서 선택되는 적어도 1종의 화합물을 이용하는 것이 더욱 바람직하다. 이들 중에서도, 4-(2,3,4-트리메톡시-6-메틸벤조일)-2,5-디클로로-3-트리플루오로메틸피리딘 및 4-(2,3,4-트리메톡시-6-메틸벤조일)-2-클로로-3-트리플루오로메틸-5-메톡시피리딘으로 이루어지는 군에서 선택되는 적어도 1종의 화합물을 이용하는 것이 가장 바람직하다.Among the compounds represented by the above formula (I-2), 4- (2,3,4-trimethoxy-6-methylbenzoyl) -2,5-dichloro-3-trifluoromethylpyridine (Compound No. 39), 4- (2,3,4-trimethoxy-6-methylbenzoyl) -2-chloro-3-trifluoromethyl-5-methoxypyridine (Compound No. 40), 4- (2,3,4 -Trimethoxy-6-methylbenzoyl) -2-bromo-3-trifluoromethyl-5-methoxypyridine (Compound No. 41), 4- (2,3,4-trimethoxy-6- Methylbenzoyl) -2,3,5-trichloropyridine (Compound No. 42), 4- (2,3,4-trimethoxy-6-methylbenzoyl) -3,5-dichloropyridine (Compound No. 43 ), 4- (2,3,4-trimethoxy-6-methylbenzoyl) -3-chloro-5-methoxypyridine (Compound No. 44), 4- (2,3,4-trimethoxy- 6-methylbenzoyl) -2-bromo-3-chloro-5-methoxypyridine (Compound No. 45) and 4- (2,3,4-trimethoxy-6-methylbenzoyl) -3-bromo Use of at least one compound selected from the group consisting of -5-methylpyridine (Compound No. 46) More preferred. Among these, 4- (2,3,4-trimethoxy-6-methylbenzoyl) -2,5-dichloro-3-trifluoromethylpyridine and 4- (2,3,4-trimethoxy-6 Most preferably, at least one compound selected from the group consisting of -methylbenzoyl) -2-chloro-3-trifluoromethyl-5-methoxypyridine is used.
본 발명의 살진균제 조성물은 특히 농원예용 살진균제로서 유용하다. 농원예용 살진균제로서는, 예를 들면 벼(Oryza sativa 등)의 도열병, 깨잎 마름병, 잎집 무늬 마름병; 보리류(Hordeum vulgare, Tricum aestivum 등)의 백분병, 붉은 곰팡이병, 녹병, 설부병(snow mold, snow blight), 겉 깜부기병, 눈무늬병, 잎마름병, 껍질 마름병; 감귤(Citrus spp. 등)의 흑점병, 더댕이병; 사과(Malus pumila)의 모닐리아병, 백분병, 반점 낙엽병, 흑성병; 배(Pyrus serotina, Pyrus ussuriensis, Pyrus communis)의 흑성병, 흑얼룩병; 복숭아(Prunus persica 등)의 회성병, 흑성병, 포모프시스 부패병; 포도(Vitis vinifera spp. 등)의 흑두병, 만부병, 백분병, 노균병; 감(Diospyros kaki 등)의 탄저병, 낙엽병; 박과류(Cucumis melo 등)의 탄저병, 백분병, 덩굴마름병, 노균병; 토마토 (Lycopersicon esculentum)의 겹둥근무늬병, 잎곰팡이병, 역병; 유채과 야채(Brassica sp., Raphanus sp. 등)의 흑얼룩병; 감자(Solanum tuberosum)의 겹둥근무늬병, 역병; 딸기(Fragaria 등)의 백분병; 여러 가지 작물의 회색 곰팡이병, 균핵(Sclerotinia)병 등의 병해의 방제에 유효하지만, 특히 보리류, 야채류의 백분병 및 벼의 도열병에 우수한 방제 효과를 나타낸다. 또한, 푸사리움균(Fusarium), 피티움균(Pythium), 리조크토니아균(Rhizoctonia), 베르티실리움균(Verticillium), 플라즈모디오포라균(Plasmodiophora) 등의 식물 병원균에 의해 야기되는 토양 병해의 방제에도 유효하다.The fungicide compositions of the present invention are particularly useful as agrohorticultural fungicides. As an agricultural horticultural fungicide, for example, rice ( Oryza sativa, etc.), sesame leaf blight, leaf blight blight; Barley ( Hordeum vulgare , Tricum aestivum, etc.), red mold, rust, snow mold, snow blight, snow blight, leaf blight, bark blight; Sunspot disease, bladder disease, citrus spp., Etc .; Apple ( Malus pumila ) monoliths, white powder, spot deciduous, blackness; Pyrus serotina , Pyrus ussuriensis , Pyrus communis ), black spot, black spot disease; Prunus persica, etc.), blackness, morphosis rot, etc .; Vitis vinifera spp. Such as blackhead disease, bloating disease, powdery mildew, Downy mildew disease; Diospyros kaki et al., anthrax, deciduous disease; Anthracnose, powdery mildew, vine blight, and downy mildew of Cucumis melo ; Rounded pattern disease, leaf fungal disease, late blight of tomato ( Lycopersicon esculentum ); Black spot disease of cress ( Brassica sp., Raphanus sp., Etc.); Potato ( Solanum tuberosum ), plaque, plague; Percent bottle of strawberries ( Fragaria et al.); It is effective in controlling diseases such as gray mold disease and Sclerotinia disease of various crops, but exhibits excellent control effect especially on barley, vegetable white powder bottle and rice blast bottle. In addition, soil diseases caused by plant pathogens such as Fusarium , Pythium , Rhizoctonia , Verticillium , Plasmodiophora , etc. It is also effective for prevention.
본 발명의 살진균제 조성물을 구성하는 복수의 유효 성분은, 종래의 농약 제제와 동일하게, 각종 보조제를 혼합하여 분말제, 입제, 과립 수화제, 수화제, 수성 현탁제, 유성 현탁제, 수용제, 유제, 액제, 페이스트제, 에어졸제, 미량 산포제 등의 여러 가지 형태로 제제하여 사용되지만, 본 발명의 목적에 적합한 한, 통상의 해당 분야에서 이용되고 있는 모든 제제 형태로 할 수 있다. 제제에 사용하는 보조제로서는 규조토, 소석회, 탄산칼슘, 탈크, 화이트 카본, 카올린, 벤토나이트, 카올리나이트 및 견운모의 혼합물, 클레이, 탄산나트륨, 중탄산 소다, 망초, 제올라이트, 전분 등의 고형 담체; 물, 톨루엔, 크실렌, 용매 나프타, 디옥산, 아세톤, 이소포론, 메틸이소부틸케톤, 클로로벤젠, 시클로헥산, 디메틸술폭시드, 디메틸포름아미드, 디메틸아세트아미드, N-메틸-2-피롤리돈, 알코올 등의 용제; 지방산염, 벤조산염, 알킬술포 숙신산염, 디알킬술포숙신산염, 폴리카르복실산염, 알킬황산에스테르염, 알킬황산염, 알킬아릴황산염, 알킬디글리콜에테르황산염, 알코올황산에스테르염, 알킬술폰산염, 알킬아릴술폰산염, 아릴술폰산염, 리그닌술폰산염, 알킬디페닐에테르디술폰산염, 폴리스티렌술폰산염, 알킬인산에스테르염, 알킬아릴인산염, 스티릴아릴인산염, 폴리옥시에틸렌알킬에테르황산에스테르염, 폴리옥시에틸렌알킬아릴에테르황산염, 폴리옥시에틸렌알킬아릴에테르황산에스테르염, 폴리옥시에틸렌알킬에테르인산염, 폴리옥시에틸렌알킬아릴인산에스테르염, 나프탈렌술폰산포르말린 축합물의 염과 같은 음이온계 계면 활성제나 전착제; 소르비탄지방산에스테르, 글리세린지방산에스테르, 지방산폴리글리세라이드, 지방산알코올폴리글리콜에테르, 아세틸렌글리콜, 아세틸렌알코올, 옥시알킬렌 블록 중합체, 폴리옥시에틸렌알킬에테르, 폴리옥시에틸렌알킬아릴에테르, 폴리옥시에틸렌스티릴아릴에테르, 폴리옥시에틸렌글리콜알킬에테르, 폴리옥시에틸렌지방산에스테르, 폴리옥시에틸렌소르비탄지방산에스테르, 폴리옥시에틸렌글리세린지방산에스테르, 폴리옥시에틸렌 경화 피마자유, 폴리옥시프로필렌지방산에스테르와 같은 비이온계 계면 활성제나 전착제; 올리브유, 케이폭유, 피마자유, 종려유, 동백유, 야자유, 호마유, 옥수수유, 미강유, 낙화생유, 면실유, 대두유, 채종유, 아마인유, 동유, 액상 파라핀 등의 식물유나 광물유 등을 들 수 있다. 이들 보조제는 본 발명의 목적에서 일탈하지 않는 한, 해당 분야에서 알려진 것 중에서 선택하여 이용할 수 있다. 또한, 증량제, 증점제, 침강 방지제, 동결 방지제, 분산 안정제, 약해 경감제, 방미제 등 통상 사용되는 각종 보조제도 사용할 수 있다. 유효 성분 화합물과 각종 보조제와의 배합 비율은 일반적으로 0.005:99.995 내지 95:5, 바람직하게는 0.2:99.8 내지 90:10이다. 이들 제제를 실제로 사용할 때에는 그대로 사용하거나, 또는 물 등의 희석제로 소정 농도로 희석하여, 필요에 따라서 각종 전착제를 첨가하여 사용할 수 있다.The plurality of active ingredients constituting the fungicide composition of the present invention may be mixed with various auxiliary agents in the same manner as conventional pesticide preparations, and include powders, granules, granulating hydrating agents, hydrating agents, aqueous suspending agents, oily suspensions, water soluble agents, and emulsions. Although it is used by formulating in various forms, such as a liquid, a paste, an aerosol, and a microdispersion agent, it can be set as all the formulation forms currently used in the said applicable field as long as it is suitable for the objective of this invention. Auxiliary agents used in the preparation include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite and mixtures of mica, clay, sodium carbonate, soda bicarbonate, manganese, zeolite and starch; Water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, Solvents such as alcohols; Fatty acid salt, benzoate, alkyl sulfo succinate, dialkyl sulfosuccinate, polycarboxylate, alkyl sulfate ester salt, alkyl sulfate, alkylaryl sulfate, alkyl diglycol ether sulfate, alcohol sulfate ester salt, alkyl sulfonate, alkyl Aryl sulfonate, aryl sulfonate, lignin sulfonate, alkyl diphenyl ether disulfonate, polystyrene sulfonate, alkyl phosphate ester salt, alkyl aryl phosphate, styryl aryl phosphate, polyoxyethylene alkyl ether sulfate ester salt, polyoxyethylene Anionic surfactants and electrodeposition agents such as alkyl aryl ether sulfates, polyoxyethylene alkyl aryl ether sulfate ester salts, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkyl aryl phosphate ester salts, and salts of naphthalene sulfonic acid formalin condensates; Sorbitan fatty acid ester, glycerin fatty acid ester, fatty acid polyglyceride, fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, oxyalkylene block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene styryl Nonionic surfactant, such as aryl ether, polyoxyethylene glycol alkyl ether, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hardened castor oil, polyoxypropylene fatty acid ester B electrodeposition agent; Olive oil, kapok oil, castor oil, palm oil, camellia oil, palm oil, horsetail oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, kerosene oil, liquid paraffin, and mineral oil. These adjuvants may be selected and used from those known in the art, so long as they do not depart from the object of the present invention. In addition, various auxiliary agents usually used, such as extenders, thickeners, anti-settling agents, cryoprotectants, dispersion stabilizers, weakening agents, and flavoring agents, can be used. The blending ratio of the active ingredient compound with the various adjuvants is generally from 0.005: 99.995 to 95: 5, preferably from 0.2: 99.8 to 90:10. When these formulations are actually used, they may be used as they are, or diluted to a predetermined concentration with a diluent such as water, and various electrodeposition agents may be added and used as necessary.
본 발명의 살진균제 조성물을 농원예용 식물에 시용하는 것을 포함하는 식물 병해의 방제 방법도 본 발명에 포함된다. 본 발명의 살진균제 조성물의 사용 농도는 대상 작물, 사용 방법, 제제 형태, 시용량 등의 차이에 따라 상이하고, 일률적으로 규정할 수 없지만, 경엽 처리인 경우, 유효 성분당 보통 0.1 내지 10,000 ppm, 바람직하게는 1 내지 2,000 ppm이다. 토양 처리인 경우에는 보통 10 내지 100,000 g/ha, 바람직하게는 200 내지 20,000 g/ha이다.Also included in the present invention is a method for controlling plant diseases comprising applying the fungicide composition of the present invention to an agricultural horticultural plant. The concentration of the fungicide composition of the present invention varies depending on the target crop, the method of use, the form of the preparation, the dosage, and the like, but cannot be defined uniformly, but in the case of foliage treatment, usually 0.1 to 10,000 ppm per active ingredient, preferably Preferably 1 to 2,000 ppm. In the case of soil treatment, it is usually 10 to 100,000 g / ha, preferably 200 to 20,000 g / ha.
본 발명의 살진균제 조성물의 여러 가지 제제, 또는 그의 희석물의 시용은 통상 일반적으로 행해지고 있는 시용 방법, 즉 산포(예를 들면 산포, 분무, 미스팅, 아토마이징, 산립, 수면 시용 등), 토양 시용(혼입, 관주 등), 표면 시용(도포, 분의, 피복 등) 등에 의해 행할 수 있다. 또한, 이른바 초 고농도 소량 산포법(ultra low volume)에 의해 시용할 수도 있다. 이 방법에서는 활성 성분을 100 % 함유하는 것이 가능하다.The application of the various formulations of the fungicide composition of the present invention, or diluents thereof, is usually carried out by application methods which are generally carried out, ie, spraying (for example, spraying, spraying, misting, atomizing, granulating, sleeping application, etc.), soil application. (Mixing, irrigation, etc.), surface application (coating, powder coating, etc.), etc. can be performed. It can also be applied by a so-called ultra high concentration and small low dispersion method. In this method, it is possible to contain 100% of the active ingredient.
본 발명의 살진균제 조성물에서, (a)의 화학식 I로 표시되는 벤조일피리딘 유도체 또는 그의 염과 (b)의 다른 살진균제와의 적당한 혼합 중량비는 일반적으로 1:10,000 내지 10,000:1, 바람직하게는 1:1,000 내지 1,000:1, 더욱 바람직하게는 1:200 내지 200:1이다.In the fungicide composition of the present invention, a suitable mixing weight ratio of the benzoylpyridine derivative represented by the formula (I) of (a) or a salt thereof with other fungicides of (b) is generally 1: 10,000 to 10,000: 1, preferably 1: 1,000 to 1,000: 1, more preferably 1: 200 to 200: 1.
<실시예><Examples>
다음으로 본 발명에 관련된 시험예를 기재하였지만, 이들은 본 발명을 한정하는 것은 아니다.Next, although the test example concerning this invention was described, these do not limit this invention.
<시험예 1><Test Example 1>
소맥 백분병 예방 효과 시험Wheat powdery mildew prevention test
직경 7.5 cm의 플라스틱 화분에서 소맥(품종: 농림 61호)을 재배하고, 1.5 엽기에 달했을 때에 각 공시 화합물을 소정 농도로 조정한 혼합 약액 10 mL를 스프레이 건으로 1000 L/ha에 상당하도록 산포하였다. 약액이 건조된 후, 소맥 백분병균(Erysiphe graminis)의 분생 포자를 뿌려서 접종하고, 20 ℃의 항온 챔버에 유지시켰다. 접종 6 내지 8일 후에 포자 형성 면적을 조사하고, 하기 계산식에 의해 발병률을 구하여, 그 결과를 표 1 내지 표 4에 나타내었다. 또한, 무처리구의 평균 병반 면적은 약액 대신에 물을 스프레이 건으로 산포한 것 이외에는 처리구와 동일한 조작을 행함으로써 구하였다.Wheat (cultivar No. 61) was cultivated in a plastic pot of 7.5 cm in diameter, and when it reached 1.5 blade stage, 10 mL of the mixed chemical liquid in which each compound was adjusted to a predetermined concentration was sprayed to correspond to 1000 L / ha with a spray gun. After the medicine is dried, Erysiphe Conidia spores of graminis ) were sprayed and inoculated and kept in a constant temperature chamber at 20 ° C. 6 to 8 days after the inoculation, the sporulation area was examined, and the incidence rate was determined by the following formula, and the results are shown in Tables 1 to 4. In addition, the average lesion area of an untreated tool was calculated | required by performing the same operation as the process tool except having sprayed water with a spray gun instead of a chemical liquid.
발병률=(a/b)×100Incidence = (a / b) × 100
a: 처리구의 평균 병반 면적a: average lesion area of the treatment zone
b: 무처리구의 평균 병반 면적b: mean lesion area of untreated area
콜비식에 의해 이론값을 계산하였다. 실험값이 이론값보다도 낮은 경우에, 본 발명의 살진균제 조성물은 소맥 백분병 예방 효과 시험에 관하여 상승 효과를 갖는다. 이와 같은 경우에서의 콜비식에 의한 이론값을 표 1 내지 표 4의 ( )안에 함께 나타내었다.The theoretical value was calculated by Colby's formula. When the experimental value is lower than the theoretical value, the fungicide composition of the present invention has a synergistic effect with respect to the wheat flour powder prevention effect test. The theoretical value by Colby's formula in such a case was shown together in () of Tables 1-4.
<< 시험예Test Example 2> 오이 2> cucumber 백분병Powder bottle 예방 효과 시험 Preventive effect test
직경 7.5 cm의 플라스틱 화분에 오이(품종: 수요(Suyo))를 재배하고, 1.5 엽기에 달했을 때에 본 발명 화합물을 소정의 농도로 조정한 혼합 약액 10 mL를 스프레이 건으로 산포하였다. 약액이 건조된 후, 오이 백분병균(Sphaerotheca cucurbitae)의 분생 포자 현탁액을 분무 접종하고, 20 ℃의 항온 챔버에 유지시켰다. 접종 9 내지 10일 후에 포자 형성 면적을 조사하고 시험예 1과 동일하게 하여 발병률을 구하고, 그 결과를 표 5 내지 표 20에 나타내었다. 무처리구의 평균 병반 면적은 약액 대신에 물을 스프레이 건으로 산포한 것 이외에는 처리구와 동일한 조작을 행함으로써 구하였다.Cucumber (variety: Suyo) was cultivated in the plastic pot of 7.5 cm in diameter, and when it reached 1.5 leaf stage, 10 mL of mixed chemical liquids which adjusted the compound of this invention to predetermined | prescribed density were sprayed with a spray gun. After the chemical liquid was dried, the conidia of spores of Cucumber Sphaerotheca cucurbitae were spray inoculated and kept in a constant temperature chamber at 20 ° C. 9 to 10 days after the inoculation, the area of spore formation was examined and the incidence was determined in the same manner as in Test Example 1, and the results are shown in Tables 5 to 20. The average lesion area of the untreated tool was determined by performing the same operation as that of the treated tool except that water was sprayed instead of the chemical liquid.
또한, 콜비식에 의한 이론값을 표 5 내지 표 20의 ( )안에 함께 나타내었다.In addition, the theoretical value by Colby's formula was shown together in () of Tables 5-20.
다음에 본 발명의 제제예를 기재하였지만, 본 발명에서의 제제량, 제형 등은 하기 제제예만으로 한정되는 것은 아니다.Next, although the formulation example of this invention was described, the formulation amount, formulation, etc. in this invention are not limited only to the following formulation example.
<제제예 1><Example 1>
(a) 카올린 78 중량부(a) 78 parts by weight of kaolin
(b) β-나프탈렌술폰산 나트륨염과 포르말린의 축합물 2 중량부(b) 2 parts by weight of a condensate of β-naphthalenesulfonic acid sodium salt with formalin
(c) 폴리옥시에틸렌알킬아릴술페이트 5 중량부(c) 5 parts by weight of polyoxyethylene alkylaryl sulfate
(d) 함수 무정형 이산화규소 15 중량부15 parts by weight of hydrous amorphous silicon dioxide
이상의 각 성분의 혼합물과, 화학식 I의 화합물과, 피라클로스트로빈을 8:1:1의 중량 비율로 혼합하여, 수화분제(wettable powder)를 얻었다.A mixture of each of the above components, a compound of formula (I), and pyraclostrobin were mixed at a weight ratio of 8: 1: 1 to obtain a wettable powder.
<제제예 2><Example 2>
(a) 화학식 I의 화합물 0.5 중량부(a) 0.5 parts by weight of a compound of formula (I)
(b) 피라클로스트로빈 0.5 중량부(b) 0.5 parts by weight of pyraclostrobin
(c) 벤토나이트 20 중량부(c) 20 parts by weight of bentonite
(d) 카올린 74 중량부(d) 74 parts by weight of kaolin
(e) 리그닌술폰산소다 5 중량부(e) 5 parts by weight of lignin sulfonic acid sodium
이상의 각 성분에 조립을 위한 적량의 물을 가하고, 혼합, 조립하여 입제를 얻었다.An appropriate amount of water for granulation was added to each of the above components, mixed and granulated to obtain granules.
<제제예 3><Example 3>
(a) 화학식 I의 화합물 2 중량부(a) 2 parts by weight of a compound of formula I
(b) 피라클로스트로빈 3 중량부(b) 3 parts by weight of pyraclostrobin
(c) 탈크 95 중량부(c) 95 parts by weight of talc
이상의 각 성분을 균일하게 혼합하여 분말제(dust)를 얻었다.Each of the above components was mixed uniformly to obtain a powder.
Claims (12)
<화학식 I>
[식 중, A가 -N=인 경우, B는 -CX4=이고; A가 -CH=인 경우, B는 -N=이고; X1 및 X2는 각각 독립적으로 할로겐 원자, 알콕시기, 수산기, 알킬기, CF3기 또는 알킬티오기이고; X3은 수소 원자, 할로겐 원자, 알콕시기, 알킬기, CF3기 또는 알킬티오기이고; X4는 수소 원자, 할로겐 원자, 알콕시기, 알킬기, CF3기 또는 알킬티오기이고; R1은 알킬기이고; R2'은 알콕시기이고; p는 0, 1 또는 2이고; R2'' 및 R2'''은 각각 알콕시기임]
<화학식 II>
(a) a benzoylpyridine derivative represented by the formula (I) or a salt thereof, and (b) pyraclostrobin, boscalid, penthiopyrad, pyribencarb, meptyldinocap, difenokazole, dodine, sulfur, fluti Ani, containing at least one fungicide selected from the group consisting of 6-t-butyl-8-fluoro-2,3-dimethylquinolin-4-yl acetate and the compound represented by the formula (II) as an active ingredient A fungicide composition, characterized in that.
<Formula I>
[Wherein A is -N =, B is -CX 4 =; When A is -CH =, B is -N =; X 1 and X 2 are each independently a halogen atom, an alkoxy group, a hydroxyl group, an alkyl group, a CF 3 group or an alkylthio group; X 3 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF 3 group or an alkylthio group; X 4 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF 3 group or an alkylthio group; R 1 is an alkyl group; R 2 ' is an alkoxy group; p is 0, 1 or 2; R 2 '' and R 2 ''' are each an alkoxy group]
<Formula II>
<화학식 II>
The fungicide of claim 1, wherein the fungicide of (b) consists of pyraclostrobin, boscalid, penthiopyrad, pyribencarb, meptyldinocap, difenocazole, dodine, sulfur and a compound represented by formula (II). At least one fungicide composition selected from the group.
<Formula II>
<화학식 II>
The compound according to claim 1, wherein the fungicide of (b) is composed of pyraclostrobin, boscalid, penthiopyrad, pyribencarb, meptyldinocap, difenokazole, sulfur and a compound represented by formula (II). At least one selected fungicide composition.
<Formula II>
<화학식 I-1>
[식 중, X1 및 X2는 각각 독립적으로 할로겐 원자, 알콕시기, 수산기, 알킬기, CF3기 또는 알킬티오기이고; X3은 수소 원자, 할로겐 원자, 알콕시기, 알킬기, CF3기 또는 알킬티오기이고; R1은 알킬기이고; R2'은 알콕시기이고; p는 0, 1 또는 2이고; R2'' 및 R2'''은 각각 알콕시기임]The fungicide composition according to claim 1, wherein the benzoylpyridine derivative is a compound represented by the formula (I-1).
<Formula I-1>
[Wherein, X 1 and X 2 are each independently a halogen atom, an alkoxy group, a hydroxyl group, an alkyl group, a CF 3 group or an alkylthio group; X 3 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF 3 group or an alkylthio group; R 1 is an alkyl group; R 2 ' is an alkoxy group; p is 0, 1 or 2; R 2 '' and R 2 ''' are each an alkoxy group]
<화학식 I-2>
[식 중, X1 및 X2는 각각 독립적으로 할로겐 원자, 알콕시기, 수산기, 알킬기, CF3기 또는 알킬티오기이고; X3은 수소 원자, 할로겐 원자, 알콕시기, 알킬기, CF3기 또는 알킬티오기이고; X4는 수소 원자, 할로겐 원자, 알콕시기, 알킬기, CF3기 또는 알킬티오기이고; R1은 알킬기이고; R2'은 알콕시기이고; p는 0, 1 또는 2이고; R2'' 및 R2'''은 각각 알콕시기임]The fungicide composition according to claim 1, wherein the benzoylpyridine derivative is a compound represented by the formula (I-2).
<Formula I-2>
[Wherein, X 1 and X 2 are each independently a halogen atom, an alkoxy group, a hydroxyl group, an alkyl group, a CF 3 group or an alkylthio group; X 3 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF 3 group or an alkylthio group; X 4 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF 3 group or an alkylthio group; R 1 is an alkyl group; R 2 ' is an alkoxy group; p is 0, 1 or 2; R 2 '' and R 2 ''' are each an alkoxy group]
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2016
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2019
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